Search Condo Rentals in Winter Haven

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Winter Haven condo rentals

3.0 star property
8.6 out of 10, Excellent, (3142)
"Great place to stay"
United States
Jose
The price is AED 365
AED 506 total
includes taxes & fees
13 Jan - 14 January 2026
Vacation Village Orlando, Celebration
2.0 star property
10.0 out of 10, Exceptional, (3)
"Great view, comfortable room for our one night stay."
United States
Vern H.
The price is AED 352
AED 468 total
includes taxes & fees
14 Jan - 15 January 2026
Lake View•Gardens•Private Balcony Suite•Legoland
9.4 out of 10, Exceptional, (86)
"This place was awesome! Incredibly clean floors. I even called my sister just to show her how clean the floors were. "
United States
Elizabeth P L.
The price is AED 184
AED 624 total
includes taxes & fees
4 Jan - 5 January 2026
Dazzling Newly Renovated Condo 1.5 miles to Disney
10.0 out of 10, Exceptional, (1)
"Nice place in a great area. Plenty of restaurants nearby. We were evacuating from St Pete ahead of Milton with my wife, MIL and cat. Both bedrooms were nice and MIL and kitty really enjoyed the large couch in the living room. "
United States
David K.
The price is AED 275
AED 1,244 total
includes taxes & fees
5 Jan - 6 January 2026
Newly Remodeled 2-bedroom Family-sized condo 15 minutes to the theme park
10.0 out of 10, Exceptional, (1)
"Had an amazing stay! Property was exactly how it was described- clean, comfortable, very safe. (As a solo woman traveling alone feeling safe always makes a trip easier) The bed and sheets were sooo comfortable! Micki was kind, attentive, incredibly responsive and happily accommodated me, making my entire experience was seamless. I felt right at home, would happily return. 5 Stars is not enough to describe how wonderful Micki is as host!"
United States
Anonymous traveler
The price is AED 424
AED 549 total
includes taxes & fees
13 Jan - 14 January 2026
Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
10.0 out of 10, Exceptional, (1)
"The condo is ideally located for Disney World with many restaurants close by. The property manager was quick to respond to any questions and we would definitely stay there again."
United States
Michael G.
The price is AED 222
AED 1,303 total
includes taxes & fees
4 Jan - 5 January 2026
Parkway Palms Resort 1 bedroom condo mins to Disney World.
2.0 star property
10.0 out of 10, Exceptional, (1)
"The host was very nice and helpful The rooms were very clean Enjoyed our stay Would stay again"
United States
Anonymous traveler
The price is AED 272
AED 1,287 total
includes taxes & fees
24 Jan - 25 January 2026
Resort stay~Pool Access~Peaceful Retreat~Balcony
10.0 out of 10, Exceptional, (12)
"Enjoyed everything!"
United States
Caroline W.
The price is AED 248
AED 1,070 total
includes taxes & fees
5 Jan - 6 January 2026
BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️
9.6 out of 10, Exceptional, (51)
"This was a beautiful property with all the amentities and space. "
United States
Derica N.
The price is AED 413
AED 1,349 total
includes taxes & fees
2 Jan - 3 January 2026
Reunion Resort - Near Theme Parks & Airport

Condo in Champions Gate

Near Disney/Resort Pool, Bar & Gym
9.2 out of 10, Wonderful, (5)
"The property was great.. very clean and relaxing"
Canada
Dawn D.
The price is AED 323
AED 1,057 total
includes taxes & fees
19 Jan - 20 January 2026
Near Disney/Resort Pool, Bar & Gym
10.0 out of 10, Exceptional, (1)
"Wonderful location and great accommodations."
United States
Frank L.
The price is AED 364
AED 901 total
includes taxes & fees
1 Jan - 2 January 2026
Spacious condo near Walt Disney parks & AdventHealth - Kissimmee Florida
9.2 out of 10, Wonderful, (150)
"Great place! Close to everything we wanted to do, hosts were easy to communicate with, place was clean and the community felt safe and secure as a woman traveling with her kiddo. I would absolutely stay again!"
United States
Hope M.
The price is AED 220
AED 744 total
includes taxes & fees
4 Jan - 5 January 2026
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Condo in Kissimmee

Sophisticated Retreat
9.4 out of 10, Exceptional, (6)
"Amazing! I will be staying here again!"
United States
MikeD
The price is AED 309
AED 716 total
includes taxes & fees
12 Jan - 13 January 2026
Sophisticated Retreat
10.0 out of 10, Exceptional, (1)
"This 2 bedroom apartment was perfect for us. Clean and well kept. Very spacious rooms with comfortable beds. I would recommend this place. "
United States
Samuel L.
The price is AED 334
AED 991 total
includes taxes & fees
6 Jan - 7 January 2026
Family-Friendly Condo with Pool & Sauna
10.0 out of 10, Exceptional, (6)
"Nice neighborhood, local pool and condo. Would stay again."
United States
Jason M.
The price is AED 275
AED 842 total
includes taxes & fees
14 Jan - 15 January 2026
Valentina’s Condo-Resort Style!
9.6 out of 10, Exceptional, (29)
"Host was very communicative, simple check in & check out. Will stay again at this property. "
United States
Anonymous traveler
Splendid Renovated 2 + 2 Condo Near Disney with Amazing Amenities
8.0 out of 10, Very Good, (4)
"Location, privacy, security all as desired."
United States
Thomas S.
The price is AED 275
AED 715 total
includes taxes & fees
11 Jan - 12 January 2026
Lake View, Heated Pool, King Bed, Free Parking, Resort Condo.
2.0 star property
9.2 out of 10, Wonderful, (7)
"It is a beautiful house, very clean, with all its comforts, 100% recommended. ❤️"
United States
Ana C.
The price is AED 371
AED 1,356 total
includes taxes & fees
11 Jan - 12 January 2026
Upstay Champions Gate Home w Private Pool & BBQ
10.0 out of 10, Exceptional, (4)
"We did a quick overnight. The condo was beautifully decorated and very clean. Location was great and close to everything. The host Elle was wonderful and quick to respond with questions. We would definitely stay here again. "
United States
Harold W.
The price is AED 380
AED 811 total
includes taxes & fees
3 Jan - 4 January 2026
Luxury Condominium in Kissimmee Florida near Walt Disney World
10.0 out of 10, Exceptional, (1)
The price is AED 296
AED 973 total
includes taxes & fees
27 Jan - 28 January 2026
5 Min to Disney! 2BR Condo w/ King Bed, Pool, Fast WiFi & SmartTV+kitchen+washer
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Haven Hotel Reviews

Frequently asked questions

How much do condos in Winter Haven cost?
Condos in Winter Haven range from AED 468 to AED 1,349 per night. These stays offer loads of space for the entire family at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Winter Haven?
Work out your vacation dates and then pick from 3445 condos in Winter Haven. For official business travel, a weekend escape or anything in between, Expedia can help you find the right place in just a few clicks.
Why book your condo in Winter Haven with Expedia?
Reserving a condo in Winter Haven is as easy as clicking on your travel dates and picking an option that suits your style. After something inexpensive or upscale, or a stay that also comes with a kitchen and laundry? Use Expedia's search filters to narrow your results even further and find your ideal match.
How can I find cheap condos in Winter Haven?
The simplest way to track down cheap condos in Winter Haven is with Expedia's convenient filter tool. Refine your search results by budget, amenities and star rating to discover unbeatable deals in just a few clicks.